(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate → HCID 11165987, compound

HRID 1261863Notes

Reaction equation

HRID 1261863 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@H:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2]>C(#N)C.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:22])[C@H:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 11120686(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Product 1

HCID 11165987HCID 11165987, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

1.3 g of N-tert.-butyloxycarbonyl-L-glutamic acid 5-methyl ester 1-tert.-butyl ester (1.2., 4.12 mmol) are dissolved in 15 ml of acetonitrile and mixed with 100 mg of N,N-dimethyl-4-aminopyridine (DMAP). A solution of 1.79 g of di-tert.-butyl-bicarbonate (8.2 mmol) in 7 ml of acetonitrile is added under nitrogen atmosphere. After stirring overnight, the solvent is removed under vacuum and the crude product obtained is purified by means of chromatography on silica gel.

Workup

  1. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-2d47b6e10ee64082a749909633f77075
Source dataset
uspto-grants-2013_06
Patent number
US08471063B2

Reaction notes

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